Patent GB-945890-A (GB)
Title: New pyrimidine dyestuffs
Inventor: ANDREW HERBERT FRANCIS
IPC: C09B62/20
Filed: 1960-09-12
Abstract: The invention comprises dyestuffs which contain at least one group of the formula <FORM:0945890/C3/1> wherein A represents -O-, -S- or <FORM:0945890/C3/2> , R represents a hydrogen atom or a substituted or unsubstituted alkyl radical, Y represents a chlorine or bromine atom and V represents an amino or substituted amino group and a process for the production thereof which comprises reacting 5 - cyano - 2 : 4 : 6 - trichloropyrimidine or 5 - cyano - 2 : 4 : 6 - tribromopyrimidine with a dye containing at least one -AH group where A has the meaning given above and with ammonia or a primary or secondary amine, one molecular proportion of the pyrimidine and one molecular proportion of ammonia or the primary or secondary amine being used for each -AH group present in the dye.  In a modified process for the production of an azo dye by diazotization and coupling either the primary amine or coupling component or both contain at least one group of the formula given above.  Dyes containing -AH groups described in the parent Specification may be used as starting materials in the process. Representative of amino groups represented by V are methylamino, N - methyl - N - n - propylamino groups which may contain such substituents as hydroxy, methoxy, phenyl, cycloalkylamino groups, e.g. cyclohexylamino groups, arylamino and N-alkyl-N-arylamino groups, e.g. anilino or N-methylanilino, 2, 3 or 4-methoxyanilino, 2 : 5- or 3 : 5-disulphoanilino, 2, 3 or 4-carboxyanilino and sulpho- or disulphonaphthylamino groups.  Amines specified for use in the process include N,N - di - b  - hydroxyethylamine, N-methyl - N - b - methoxyethylamino b  - phenylethylamine, piperidine and morpholine. Dyes are prepared in examples by reacting the trisodium salt of 1-amino-4-(41-aminoanilino) anthraquinone 2 : 31 : 5-trisulphonic acid with the product obtained by reacting metanilic acid with 5 - cyano - 2 : 4 : 6 - trichloropyrimidine (1); the sodium salt of copper phthalocyanine-3-sulphon - N - (41 - aminophenyl) amide - 3 - sulphonamide-3-sulphonic acid with the product obtained by reacting 5-cyano-2 : 4 : 6-trichloropyrimidine with sodium metanilate or disodium aniline 2 : 5 - disulphonate (2, 3); 4 - ethoxy-31 - amino - 2 - nitro - diphenylamine - 41 - sulphonic acid with the product obtained by reacting sodium metanilate with 5-cyano-2 : 4 : 6-trichloropyrimidine (4); sodium metanilate with the product obtained by reacting 2-methylamino - 5 - hydroxy - 6 : 21 - azonaphthalene-7 : 11 : 51-trisulphonic acid with 5-cyano-2 : 4 : 6 - trichloropyrimidine (5); 1 - aminobenzene-4-sulphonic acid with the product obtained by reacting 5-cyano-2 : 4 : 6-trichlor with the trisodium salt of 6-N-methylamino-1-hydroxy - 2 : 21 - azonaphthalene - 11 : 3 : 51-trisulphonic acid (6); by employing 5-cyano-2 : 4 : 6-tribromopyrimidine instead of the trichloro compound in a similar process (7) and in place of the trisodium salt used in (6) the tetrasodium salt of the copper complex of 2 - amino - 6 - [21 - methoxy - 51 - methyl - 41-(211,511 - disulphophenylazo) phenylazo] - 5 - naphthol-1 : 7-disulphonic acid and in place of the sodium salt of 1-aminobenzene-sulphonic acid the disodium salt of 5-sulpho-2-aminobenzoic acid (8).  The dyes are employed to colour cellulose textile materials.  The Provisional Specification also relates to dyes of similar formula to that given above in which the -CN group is replaced by the carboxy or carbalkoxy group.